Stereoselective double reduction of α,β-unsaturated imines

Many natural and biologically active compounds feature at least one amine function, often accompanied by multiple asymmetric centers. While numerous methodologies have been developed to synthesize these chiral amines, existing approaches suffer from significant limitations: they are either sequential with poor diastereoselectivity control, restricted to producing a single stereoisomer, or capable of controlling only one asymmetric center at a time.This project aims to address these challenges by achieving the fully controlled, stereoselective double hydrogenation of α,β-unsaturated imines using dual catalysis. A key advantage of this methodology is its ability to simultaneously control up to three asymmetric centers in a stereodivergent manner. While chemoselective reductions of either imine groups or C=C double bonds in α,β-unsaturated ketones have been explored by other research groups, no precedent exists for the proposed double reduction of α,β-unsaturated imines.

The success of this project hinges on the synergistic use of two distinct catalysts: one specialized for reducing the double bond and another for imine reduction. This interdisciplinary effort will be made possible through a collaboration between the SERCO team at DCM, experts in organic synthesis, and the PMB team at LCBM, specialists in the synthesis and characterization of organometallic complexes.

Ultimately, this innovative methodology will enable the synthesis of optically active amines with biological relevance by controlling all newly formed asymmetric centers through the development of chemoselective catalysts.

The PhD will be conducted in two laboratories of Grenoble:

In the SERCO team at DCM located in UGA. 

In the PMB team at LCBM located in CEA.

An appropriate background for the candidate includes a Master in organic and/or inorganic chemistry with some experience in these fields. Additional experience in catalysis and stereoselective reactions would be advantageous.